[![Image]() Meet Jobicy Copilot — free AI autofill for job applications + remote job alerts ›](#) [All remote jobs](https://jobicy.com/jobs.md)Open role[![Help Scout logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2021/01/WRILS-210106163921-999274.jpg)](https://jobicy.com/company/help-scout.md)Remote opportunity at[Help Scout](https://jobicy.com/company/help-scout.md) # Head of Product, Conversations Review the role, location requirements, compensation details, and application process before deciding whether this opportunity fits your next career move. [Apply for this job](#job-application)[View company](https://jobicy.com/company/help-scout.md)Share14 Sep 2026Published78Listing views4Application actions14 Oct 2026Apply before Opportunity details ## About this role. AI SummaryHelp Scout is seeking a senior product leader to own the Conversations group, covering its Inbox workspace and AI-powered Copilot product lines. The role owns product vision, roadmap, monetization, revenue outcomes, and the customer experience for a core B2B SaaS surface. This player/coach leader will work hands-on on strategy and prioritization while hiring, managing, and developing product managers. Success requires strong AI product judgment, commercial and packaging expertise, customer research, analytics, technical fluency, and cross-functional leadership with engineering, GTM, customer success, and the Autonomy group. The position is fully remote but restricted to US-based applicants. ## Role DNA A quick view of the complexity, pace, ownership and collaboration implied by the job description. ### Job Complexity 5/5EasyHard ### Pace & Pressure 5/5RelaxedFast-paced ### Autonomy Level 5/5GuidedFull ownership ### Communication Load 5/5IndependentCollaborative AI insightThis is an executive-level, revenue-accountable product leadership role for the company’s most-used product area. It requires balancing AI strategy, daily-use product quality, monetization, cross-team platform dependencies, and people leadership in a high-ownership environment. ## Salary analysis Estimated compensation compared with the broader US market for similar roles. Estimated job medianMarket rate$276,500US market range$240k–$330k0$363k AI insightThe disclosed annual base salary range is USD 263,000–290,000, with a midpoint of USD 276,500. The estimated US market range for a Head of Product leading a core B2B SaaS and AI product group is approximately USD 240,000–330,000 annually, depending on company stage, scope, location, and equity or variable-compensation structure. ## Core skills Skills and capabilities most closely associated with this opportunity. [Product strategy](https://jobicy.com/jobs?search_keywords=Product%20strategy.md)[B2B SaaS](https://jobicy.com/jobs?search_keywords=B2B%20SaaS.md)[AI product management](https://jobicy.com/jobs?search_keywords=AI%20product%20management.md)[Product monetization](https://jobicy.com/jobs?search_keywords=Product%20monetization.md)[Roadmap ownership](https://jobicy.com/jobs?search_keywords=Roadmap%20ownership.md)[People management](https://jobicy.com/jobs?search_keywords=People%20management.md)[Customer research](https://jobicy.com/jobs?search_keywords=Customer%20research.md)[Product analytics](https://jobicy.com/jobs?search_keywords=Product%20analytics.md)[Cross-functional leadership](https://jobicy.com/jobs?search_keywords=Cross-functional%20leadership.md)[Technical product fluency](https://jobicy.com/jobs?search_keywords=Technical%20product%20fluency.md) Sample interview questionsHow would you create a unified product strategy for Inbox and Copilot while ensuring AI improves rather than disrupts support workflows?I would begin with direct observation and research into the highest-frequency support workflows, identifying points where context gathering, drafting, routing, and follow-up create meaningful effort. I would define a shared experience strategy centered on human control, clear confidence signals, fast review, and measurable improvements in resolution quality and time. The roadmap would prioritize connected workflows rather than isolated AI features, with adoption, acceptance, time-to-resolution, and customer-satisfaction metrics validating each investment. Describe how you would approach monetization for a product group that includes seat-based software and AI usage. I would segment customers by support complexity, volume, team maturity, and realized AI value to understand willingness to pay. I would create packaging that keeps the core workspace accessible while aligning AI pricing with tangible outcomes, such as increased capacity, faster resolution, or advanced automation. Before scaling a model, I would pressure-test it with usage data, qualitative customer interviews, sales feedback, margin analysis, and controlled packaging experiments. How do you lead product managers while remaining hands-on in a player/coach role? I set explicit decision rights, outcomes, and product-quality standards, then give PMs meaningful ownership of problem spaces. My coaching focuses on sharpening customer understanding, strategic framing, analytical rigor, and written decision-making rather than taking work back from them. I stay personally involved in the highest-leverage strategic choices, complex cross-functional dependencies, senior stakeholder alignment, and talent development. What metrics would you use to evaluate the success of Copilot in a customer-support product? I would use a balanced scorecard that includes adoption, suggestion exposure, draft acceptance and edit rates, time to first response, time to resolution, quality assurance outcomes, and customer satisfaction. I would segment the data by customer type, channel, workflow, and agent tenure to distinguish genuine value from superficial feature usage. I would also monitor failure modes, including incorrect suggestions, low-confidence contexts, and instances where AI creates additional review burden. Tell us how you would manage a shared dependency with another product group, such as an AI agent platform. I would establish a joint customer experience narrative, shared success metrics, clear ownership boundaries, and a regular operating cadence for roadmap and launch decisions. The teams should jointly own customer-facing seams, even where the underlying technical components have separate accountable leaders. When priorities conflict, I would use customer impact, strategic value, delivery risk, and economic impact to make tradeoffs explicit and resolve them quickly. ### Who we are Help Scout started in 2011 with a simple premise: support software should treat customers like people, not tickets. 3+ billion conversations later, more than 10,000 companies use Help Scout to grow relationships with customers of all types, from clients to patients and beyond. Now we’re in a new chapter: not only building AI that gives teams more space to focus on the customer experience, but also reimagining how we operate in an AI-native world. That means shipping and learning faster, without compromising on craft. Great work here carries a strong opinion and sweats the details, regardless of the tools we use to drive it. We’ve been a [fully remote team](https://articles.helpscout.com/blog/remote-culture/) since day one, with 120+ teammates now all over the world. It’s a culture where you’ll be trusted to take ownership, stay curious, and raise the quality of work around you. It comes with clear expectations and a team that will push you to do some of the best work of your career. If that kind of challenge gives you energy, we’d love to meet you. ### Your impact Help Scout has earned something most software companies never get: genuine trust. 10,000+ businesses use us because we’ve always believed that customer relationships are the business, and that every interaction should feel like it came from someone who cares. That trust took a decade to build, and now it’s the foundation for something bigger. The support industry is changing shape. AI will take on more of the tedious work so humans can lean into the relationship part. At Help Scout, the place where that relationship actually happens is the Conversations product group, which spans two product lines. Inbox is the workspace: every channel and every conversation in one place, built for the people who spend their whole day inside it. Copilot is AI working alongside them: drafts ready to review, context at their fingertips, and the tedious parts handled so every reply is faster and better. Conversations is the most-used surface we have. This is where every user spends most of their day, so speed, reliability, and craft are the product. It’s also where the rest of the platform becomes real: Agent hands conversations to humans at the right moment, customer context shows up right where the work happens, and every one of those moments either builds trust or spends it. You’ll be accountable for bringing it all to life with clarity and impact. ### About the role You’ll own the Conversations product group end to end: vision, roadmap, monetization, and results for the Inbox and Copilot product lines. You’ll report to Scott Rocher, our Chief Product Officer, and you’ll be accountable for the revenue growth of the group. This is a player/coach role. Inbox and Copilot are the surfaces our customers touch most, the core of the business today and the front door to everything we build next. You’ll do the strategic product work on them yourself: deciding what needs to get built next, how the workspace and its AI evolve together, and where investment in craft pays off. As the group grows, you’ll hire and manage a team of PMs. Note: This role is open to US-based applicants only. ### What you’ll do * Set the vision and strategy for the Conversations group, and decide how Inbox and Copilot evolve together as one experience where AI makes every support pro faster without breaking their flow. * Drive the Inbox roadmap hands-on: the workspace where every channel comes together and where our users spend their time in the product. This surface is held to a bar where speed, reliability, and polish are a differentiator. * Drive the Copilot roadmap hands-on: integrations, contextual summaries, suggestions, and in-the-moment assistance that make each person on a support team meaningfully better at their job. * Own how your products are monetized. Conversations spans seats and AI usage, and you’ll design the packaging that makes each seat more valuable as Copilot does more. You’ll collaborate with partners across Help Scout to model the impact of the products you ship. * Partner deeply with the Autonomy group. Significant parts of Copilot run on the agent platform, and likewise, Agent hands conversations to humans in your workspace. The seams between the two groups are owned jointly, and making them invisible to customers is part of the job. * Spend real time with customers, understanding how support pros and their leaders actually work, where AI helps, and where it gets in the way * Partner with GTM and CS so the Conversations story is clear, the adoption motion is tight, and customer feedback loops back into the roadmap * Build and manage the Conversations PM team as it grows, coaching for judgment and raising the bar for product craft across the group ### What we’re looking for * You’ve owned a core product at scale, the kind people spend their whole workday in, and you’re as fluent in the commercial side of product as you are in features and user experience * You’ve shipped AI-powered products and you understand how they succeed and fail * You collaborate well across ownership lines. Copilot ships on technology the Autonomy group builds, and you know how to co-own a product surface with a peer and keep the seams invisible to customers * You think in outcomes. Time to resolution, drafts accepted, teams that get more efficient as they use more of Help Scout . * You care about craft. You notice the details that make daily-use software feel fast, calm, and reliable, and you hold a roadmap accountable to them * You have strong monetization instincts. You can package a product line that spans seats and outcomes, and explain the tradeoffs. * You’ve managed product managers before and still love doing the work yourself. You know how to coach without taking over, and you know when a decision is yours to make * You’re data self-sufficient. You pull your own data, run your own analyses, and use numbers to pressure-test direction * You’re technically fluent enough to build genuine trust with engineers. You can hold a meaningful conversation about system architecture and make better decisions because of it * You’re fluent with AI tools and treat them as part of your craft, for research synthesis, strategy testing, rapid prototyping, and customer signal analysis. You have a point of view on where these tools are heading and how they’re changing the shape of product work * You understand that when execution is cheap, judgment is the bottleneck. Your highest-leverage hours go to strategy and prioritization, defining what’s next and what’s not * You’re an excellent writer. Help Scout runs on writing, and you make your thinking visible in one-pagers, briefs, and narratives that move decisions forward * You’ve worked in B2B SaaS and understand the difference between building for support teams and building for end consumers ### Company values ### Happy to Help Help is in our first name! We show up for each other — not out of obligation, but because we’re invested in the team’s collective success. We share knowledge freely, lead with generosity, and practice empathy with our teammates, customers, and community. ### Craft over Convention Our success relies on the quality and [craft](https://paulstamatiou.com/craft) of the work we put into the world. The status quo simply won’t work. So we insist on narrow focus, sweating every detail, and relentless pursuit of customer delight. ### Progress not Perfection Achieving our true potential — collectively and individually — requires constant progress and forward momentum. By creating a culture of curiosity and openness, we aim to create a safe space for mistakes, the ability to identify them quickly, and use them to get better. ### Own the Outcome Own the outcome means taking full responsibility for the results of your work, decisions, and contributions. It reflects a mindset of accountability, proactiveness, and follow-through. If you “own the outcome,” you don’t just complete tasks, you ensure your work leads to meaningful results, and take initiative to solve problems rather than passing them along. Read more about how we define, share, and live these values [here](https://articles.helpscout.com/blog/aligning-culture-with-values/). ### Benefits And Perks * Competitive salary and an internal, transparent salary formula based on market data * Flexible time off – you choose the holidays and vacations that make sense for you * 12 weeks of fully paid parental leave for all new parents, including adoption and foster care * A home office stipend to help you get set up and productive * A co-working stipend up to $300 a month if you choose to work out of your house * A yearly professional development stipend of $1,800 to help you grow in your craft * If you’re in the U.S. or Canada, we offer top tier health insurance for you and your dependents. ### Hiring Guidelines: All roles at Help Scout are fully remote. Some positions have specific location requirements. For roles outside the U.S. and Canada, we work with teammates as independent contractors under country-specific agreements. We do not sponsor visas. Teammates must already be authorized to work from their home country. We are an equal opportunity employer and are committed to building a company that embraces and celebrates [diversity and inclusion](https://www.helpscout.com/dei/). We do not discriminate on the basis of race, religion, color, national origin, gender, gender identity or expression, sexual orientation, age, marital status, veteran status, or disability status. We have read the studies and understand that diverse teams build better products, bring more perspective to the table, contribute to a company’s financial success, and help foster a more inclusive environment for all employees, but the bottom line is that it’s the right thing to do. To provide you with the best experience, we can support you with accommodations or adjustments at any stage of the recruitment process. Simply inform our recruitment team during your conversation with them. ### A note on the use of AI in our interview process While we understand that AI is an important tool in a modern skillset, we ask that you do not utilize AI assistants live on our interviews. Of course, use any tools you need to prepare! But we’d like for you to have a real human-to-human conversation with our team. On our end, we utilize a platform called Brighthire as a notetaker and review tool to ensure a fair and transparent hiring process. Beware of scammers! All legitimate communication from Help Scout regarding your application will come directly from an @[helpscout.com](http://helpscout.com) email address and through our applicant tracking system, Ashby. We will never ask for personal financial information or conduct interviews outside of these official channels. Show more [Apply now >](https://jobicy.com/jobs/153221-head-of-product-conversations.md) * ![Upload CV](data:image/svg+xml;base64,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) ### Upload your resume now To unlock remote work opportunities and be discovered by global employers. 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